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Palladium-Catalyzed Solid-State Polyfluoroarylation of Aryl Halides Using Mechanochemistry

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Title: Palladium-Catalyzed Solid-State Polyfluoroarylation of Aryl Halides Using Mechanochemistry
Authors: Takahashi, Rikuro Browse this author
Seo, Tamae Browse this author
Kubota, Koji Browse this author
Ito, Hajime Browse this author →KAKEN DB
Keywords: mechanochemistry
ball mill
Issue Date: 29-Nov-2021
Publisher: American Chemical Society
Journal Title: ACS catalysis
Volume: 11
Issue: 24
Start Page: 14803
End Page: 14810
Publisher DOI: 10.1021/acscatal.1c03731
Abstract: The Suzuki-Miyaura cross-coupling between poly-fluorinated arylboron nucleophiles and aryl halides enables the efficient construction of polyfluorinated structural motifs frequently found in organic materials and catalysts. A key challenge associated with this transformation involves the slow transmetalation with weakly nucleophilic polyfluorinated organoboron reagents, which often reduces the yield of the coupling products. Here, we show that solid-state high-temperature ball-milling conditions facilitate a palladium-catalyzed cross-coupling with polyfluorinated arylboronic acids and pinacol esters employing a simple catalytic system in the absence of any stoichiometric additives. This reaction exhibits a broad substrate scope and can be carried out in air, and the use of large amounts of dry and degassed organic solvents is not required. The successful cross-coupling of weakly nucleophilic polyfluorinated organoboron reagents was ascribed to the extremely high concentrations of the substrates and the catalyst under solid-state conditions.
Rights: This document is the Accepted Manuscript version of a Published Work that appeared in final form in ACS catalysis, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see
Type: article (author version)
Appears in Collections:工学院・工学研究院 (Graduate School of Engineering / Faculty of Engineering) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)

Submitter: 久保田 浩司

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